Conan O’Brien is pretty nerdy. And hot.
David Krumholtz
You want the short list or the long list? There are groups for people like you.
I can’t believe I’m the first one to mention:
Chloe O’Brian from 24
Janine Garafolo from…anything, but particularly her character in 24 this season
Pam from The Office
Michelle the Band Camp nerd from American Pie (althogh Allison Hannigan was mentioned)
also, more obscure, but Mariel Hemmingway play a nerdy ant scientist in Delerious with John Candy.
My God, it’s a real-life Kenneth from “30 Rock.”
Leila Dunbar, from Antiques Roadshow. She’s the teeny gal with the big hoarse voice who does 20th century collectibles. It would be such a kick talking vintage cars or 78 records. In bed. With a woman.
Anne Kornblut, the petite brunette Washington Post writer sometimes seen on MSNBC. She lives at the intersection of Smartest and Cutest Girl in the Class, and wears lots of red.
Mary Gross. Adorskable bang-haired gangly goof from 80s SNL.
Carol Burnett, circa 1960s. There was something arousing about how very physical her comedy was, how she used her face and body so freely, even though she wasn’t show-biz pretty.
Elaine May, circa about that same time.
Sandy Dennis, ditto.
Carolyn Faye Fox; local restaurant scribe, and inveterate punster on the NPR show Says You!.
I can’t find any good pictures online, but trust me.
Dibs.
Do cartoons count? I will always love Daria.
Now to me Stephanie Courtney and Sandy Dennis are (or were) pretty women. I wouldn’t call them nerdy simply 'cause they’re too attractive.
I’m surprised no mother has chimed in with Steve “Blues Clues”
Sandy really walked the line between pretty and awkward. I can’t decide, sometimes, when I see her photo or a film she made. All I know is I find her very appealing. Some people can’t stand her.
Kirsten Dunst. Her best friend growing up was Carl freakin’ Sagan’s daughter! The only way you get nerdier than that, is by being Sagan’s daughter (or Bill Gates’ or Steve Jobs).
Jemaine Clement and Bret McKenzie. Especially Jemaine, for me (he’s on the right in that pic).
I’m not sure about Wesley. Of course, he’s the poster boy for skillful character development, but he’s not really a nerd on Angel (well, not after the first season, I should say). He’s not sexy as a nerd, and intensely sexy as a non-nerd. Willow never stops being a nerd, and is sexy either way (though I don’t think she ever realy knows how beautiful she is).
Now Fred is inarguably a nerd and arguably hot.
Rachel Maddow counts as a nerd, right?
I don’t know but she may count as a man 
If you think so then it counts
You mean like this?
I also have an obsession with Kari, that is the single issue of Maxim I have.
My gf was poking through a bookcase and found it then dropped it spine first on the coffee table. She saw what it opened to, flipped a couple pages then said “well that makes sense”. She put it back like it was a technical book I use at work.